A couple poses together outside of Fenway Park during their Boston engagement session.

A Guide to Getting Awesome Boston Engagement Photos

During my sophomore year as a college student in New Hampshire, I lived in Boston for a summer internship. It was a great experience; I quickly learned why people love the city.

Now that I’m a wedding photographer, I welcome any chance to work with my couples on their Boston engagement session.

Here are some tips for planning your own engagement shoot in Boston.

How long is a typical engagement session?

To be useful, your engagement session should typically be at least one hour. If you have plans for multiple locations or outfits, then aim for more like 90 minutes.

As a Connecticut wedding photographer, I include an engagement session with all of my wedding photography packages. Most of the couples I work with choose a single location or venue and we spend all of our time there.

If you’re having a Boston engagement session, however, the city will literally be your playground. Be sure to talk with your photographer about scheduling adequate time. This isn’t important so much for getting more photos, but more diversity in the locations of the photos.

Tips for an Awesome Boston Engagement Session

1. Pick multiple engagement photo locations in the city

A couple stands still together as passersby are blurred from walking quickly while working on taking Boston engagement photos.

Boston is the New England’s biggest by population. All of the people who live there are doing something with their free time. So, having just one location in Boston for your engagement session might turn into a big regret later.

So the tip here is this: work with your wedding photographer and plan out multiple locations in Boston to visit for your engagement session. Try and taken in everything, from the multiple water views, historic buildings, and great parks.

During their engagement session in Boston, an engaged couple walks together and holds hands while the Kenmore Citgo sign is in the background.

To help you get some ideas, I’ve littered multiple Boston engagement photo locations throughout this post as suggestions.

2. Take the T through Downtown Boston and beyond

A couple poses underground at an MBTA subway station while waiting for a T train during their session to make Boston engagement photos.

In use since 1897, Boston’s T subway system is the focal point of transportation in the city. Its 153 stops can take you pretty much anywhere in the city.

Other than walking around during your engagement session, you should use the T. It’s better for the environment and less frustrating than driving, much cheaper than Uber, and less awkward than taking a taxi.

A T subway train drives by fast as an engaged couple hugs each other next to it while making Boston engagement photos.

Most importantly, however, taking the subway gives you more opportunities for photos during your Boston engagement session.

Some of the downtown areas of the city include Beacon Hill, the South End, and Back Bay. While you’re on the T, you can take the Red Line and get off at Park Street to visit Boston Common.

3. Consider a Boston Common engagement session

A couple poses while holdings hands in front of Ether Monument in Boston Common during their Boston engagement session.

Your gallery of engagement photos in Boston would be incomplete without going to Boston Common, located in the Beacon Hill part of the city. This is the oldest park in all of the United States (not just Massachusetts or New England, the entire country).

New York may have many more parks than Boston, but the Common definitely holds its own. From the Frog Pond, open fields, flowers, and plenty of park benches, this accessible park has plenty of features for everyone. This makes Boston Common ideal for all kinds of portraits. Another thing to note is that the Common is one of the city’s popular spots for incorporating some cherry blossoms into your engagement session.

A couple sits on the grass at Boston Common while making their Boston engagement photos with their engagement photographer.

While here, I couldn’t help but consider how beautiful Boston Common would be for a proposal. There’s plenty of space here to spread out and have a little privacy. Frankly, this park would be great whether you decide to hire a proposal photographer or photograph your own proposal.

Another idea in this area, just north of Boston Common, is Acorn Street in Beacon Hill. It’s speculated to be “the most photographed street in the country.” Be sure to check it out if you don’t mind navigating the crowds.

Now get ready to head literally right next door to Boston Public Garden.

4. Head to Boston Public Garden for engagement photographs

A bride-to-be holds onto the arm of her partner as they walk along the water in Boston Public Garden during their Boston engagement session.

Naturally, crossing Charles Street on foot from the Common to the Boston Public Garden is a must during your engagement session. It has an entrance right at the intersection of Commonwealth Avenue and Arlington Street.

In addition to beautiful trees (including great willow trees like The Barns in CT), this park is home to over 80 species of plants which the City of Boston grows in greenhouses elsewhere. It’s definitely one of the top Boston engagement photography locations.

An engaged couple works on their Boston engagement photos while embracing and kissing under a willow tree in Boston Public Garden.

Like the Common, Boston Public Garden is another one of the city’s historic places. It’s the first public botanical garden in the United States. Unlike the Roger Williams Park Botanical Garden in nearby Providence, however, the public gardens in Boston are all outdoors.

For one of their Boston engagement photos, a couple stands by the pond at Boston Public Garden and the bride-to-be rests her hand on her partner's chest.

Conveniently, Boston Common Garage is on the Public Garden side of the Common, in case you prefer driving. While you’re here for your engagement photos, be sure to check out the Boston Public Garden Suspension Bridge, swan boats, and multiple statues and monuments.

A short walk away from Boston Public Garden is the Charles River.

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My name’s Terrence and I’m a wedding photographer based in Connecticut. Use the links right here to keep in touch. When you’re ready, let’s connect!

5. Visit the Charles River during your engagement session

An engaged couple embraces while standing on grass next to the Charles River while a sailboat with a red sail goes by during their Boston engagement session.

Probably the city’s most iconic location for water views, the Charles River will not disappoint for Boston engagement photographs. It runs right through the heart of the city, from the outskirts in the western suburbs, through Cambridge to Beacon Hill, then emptying out into Boston Harbor at the North End.

During your Boston engagement session, the Charles could actually be your photo backdrop in many different ways. Here are some examples of ways to incorporate it:

While posing for their Boston engagement photos, an engaged couple kisses in front of the Charles River while paddleboarders and sailboats are on the water behind them.

And if getting on the water is your thing, consider get in the Charles River for engagement photos. Paddle Boston has multiple rental locations along the river, offering kayaking, canoeing, and paddleboarding.

Another suggestion around here is the Hatch Memorial Shell, a very unique Boston engagement photo idea. It’s right next to the Charles, just north of the Public Garden and about a 15-minute walk from Acorn Street in Beacon Hill.

An engaged couple embraces in front of the Hatch Memorial Shell during their engagement session in Boston.

As you stand at the Charles River during your engagement session though, you’ll want to take in all the sights. The Boston city skyline is one of them.

6. Incorporate the Boston city skyline

An engagement couple looks at the city skyline while standing in an esplanade during their Boston engagement session.

Boston is one the the great metropolises in New England. Therefore, no Boston engagement session would be complete without incorporating the city skyline.

A couple stands facing each other on a foot bridge over a lagoon next to the Charles River with Prudential Tower in the background while taking Boston engagement photos.

The skyscrapers and other tall city buildings in Boston are mostly centralized in Back Bay and the Financial District. In case you’re interested, some of the most iconic tall buildings in Boston to include in your engagement photos are:

The Boston city skyline is great to incorporate into an engagement session. Here, the Waterfront neighborhood is pictured at night with stoplights and cars.

Of course, incorporating the Boston skyline into your engagement session isn’t about actually visiting these buildings in person. Instead, consider heading to these areas to get the skyscrapers into the background of your photos:

On the other hand, maybe getting close to these big city buildings is exactly what you want for your engagement photos in Boston. So consider visiting Government Center and the Waterfront.

7. Head up to Government Center and the Waterfront

Quincy Market, next to Faneuil Hall, is a great place for Boston engagement photos.

If getting downtown city vibes during your Boston engagement session is a goal, then the Government Center and Waterfront areas are excellent choices.

Government Center is just east of Beacon Hill. It’s easily accessible with its own T stop on the Blue Line as well as plenty of street parking. This area is a playground for wedding photographers. Famous sites such as Boston City Hall, Post Office Square, Faneuil Hall, and Quincy Market will be great for your engagement photos.

Waterfront is home to the New England Aquarium. Additionally, Atlantic Avenue is a wide, bustling fairway that you can walk forever. Plenty of photo ops are along the way, including Christopher Columbus Park, the huge Boston Harbor Hotel archway, and the Boston Harborwalk “trail” along the water.

The Harborwalk is a great consideration for any Boston engagement session. A brick walkway off of Atlantic Avenue is pictured with a harbor behind it.

If you’re at Faneuil Hall, you might as well continue walking up on the map and visit the North End of Boston. There are some great restaurants there. Paul Revere Mall is another free public park option, too. And don’t forget North Church.

Next, hop back on the T and and let’s head to Kenmore to continue your Boston engagement in the Fenway neighborhood.

8. Chill in Fenway during your engagement session

A couple hugs each other outside of Fenway Park and The House of Blues during their Boston engagement session.

Even if you’re not fans of Red Sox games, visiting Fenway (and Kenmore) is a superb idea for your engagement session in Boston. Here, you’ll find Fenway Park, the iconic location of the New England professional sports scene for decades. The outside of the park makes for a great backdrop for your engagement photos.

A groom-to-be twirls his fiancé in front of the Fenway stadium during their Boston engagement session.
A groom-to-be twirls his fiancé in front of Fenway Park during their Boston engagement session.
A groom-to-be twirls his fiancé in front of Fenway Park while taking their Boston engagement photos.

Fortunately, the Fenway Park part of Boston is about much more than just sports. There are pubs, bars, and restaurants around. Back Bay Fens is nice park with architectural features and water. And there are at least three institutions of higher education here, with Boston University, Northeastern University, and Berklee College of Music forming a triangle in this neighborhood.

Kenmore’s famous Citgo sign is another thing to incorporate into your Boston engagement photos. I remember when I first saw it: myself and several friends were walking around after a night at work. They laughed at me when I asked, “What’s that big red thing over there?” Little did I know that many years later, I’d be capturing engagement photos underneath it.

An engaged couple embraces in front of the Kenmore Citgo sign during their Boston engagement session.

All of the tips so far have been about getting out and about. Admittedly, sometimes you just want to stay in. Next is a Boston engagement session tip for homebodies.

9. Stay home for your Boston engagement photos

A couple poses together in front of their apartment building during their Boston engagement session.

Live in Boston already? If so, it’s not a bad idea for you to consider your own home as the setting for your engagement photography.

Open your phone’s photo app right now. I bet the most photographed location is the place where you two (or one of you) call home. Photos of your Boston engagement could definitely include the two of you in your element together at home.

As I always tell my couples, your engagement session is a time to practice for your wedding day. Doing these at home is the ultimate location for your comfort. We can have fun by getting photos of you two recreating your first date, kicking back with some drinks, or just reading together.

Because home is where the heart is.

Other Boston engagement session ideas

Here are some honorable mentions for your Boston engagement photos: Boston Public Library (Back Bay), Arnold Arboretum of Harvard University (Jamaica Plain), city streets of Cambridge or Somerville.

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